Abstract:Cyanohalogenomethylidenetriphenylphosphoranes
SummaryIodo-, bromo and chlorocyanomethylidenetriphenylphosphoranes are described as well as a procedure for the in situ generation of cyanofluoromethylidenetriphenylphosphorane. These ylides are reactive towards aldehydosugars. Des quatre cyanohalogenomtthylidt.netriphCny1phosphoranes Ph,P =C(Hal)CN, seul le derive brome 4 avait t t C partiellement dkcrit [2]. Nous rapportons la preparation en bon rendement et l'isolement i l'etat pur de ses analogues chlore 3 et … Show more
“…Treatement of 4 with commercial cyanomethylenetriphenylphosphorane gave 5 in good yield (91%). Analogue 6 was obtained by the same procedure using cyanochloromethylenetriphenylphosphorane (87%). 1 2 1 Time-dependent inactivation of AdoHcy hydrolase with ( E )-1 (panel a), ( Z )-1 (panel b), and ( E )-2 (panel c).…”
6'-Cyano-5',6'-didehydro-6'-deoxyhomoadenosine (E)-1, (Z)-1, and 6'-chloro-6'-cyano-5',6'-didehydro-6'-deoxyhomoadenosine (E)-2 were synthesized and tested as new mechanism-based inhibitors of AdoHcy hydrolase. Nucleoside (E)-1 was identified as a type I inhibitor of the enzyme, whereas inactivation of the enzyme by nucleosides (Z)-1 and (E)-2 was accompanied by the formation of a covalent labeling of AdoHcy hydrolase.
“…Treatement of 4 with commercial cyanomethylenetriphenylphosphorane gave 5 in good yield (91%). Analogue 6 was obtained by the same procedure using cyanochloromethylenetriphenylphosphorane (87%). 1 2 1 Time-dependent inactivation of AdoHcy hydrolase with ( E )-1 (panel a), ( Z )-1 (panel b), and ( E )-2 (panel c).…”
6'-Cyano-5',6'-didehydro-6'-deoxyhomoadenosine (E)-1, (Z)-1, and 6'-chloro-6'-cyano-5',6'-didehydro-6'-deoxyhomoadenosine (E)-2 were synthesized and tested as new mechanism-based inhibitors of AdoHcy hydrolase. Nucleoside (E)-1 was identified as a type I inhibitor of the enzyme, whereas inactivation of the enzyme by nucleosides (Z)-1 and (E)-2 was accompanied by the formation of a covalent labeling of AdoHcy hydrolase.
Die Reaktion des Phosphorans I (Ia) mit tert.‐Butylhypochlorit in CH2Cl2 bei ‐70°C unter N2 liefert die chlorsubstituierten Verbindungen (Ib), während die übrigen Produkte (Ib) durch Umsetzung von Cyanomethyltriphenylphosphoniumchlorid mit Brom bzw. Iod in CH2Cl2 in Gegenwart von Triethylamin erhalten wurden.
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